Isoxazolidines are structurally important scaffolds in many natural products and bioactive compounds. Herein, we report a novel synthetic method for isoxazolidine derivatives through visible-light-induced photoredox cascade cyclization of nitroarenes with triethylamine under aerobic conditions. The resultant 5-hydroxyl isoxazolidine compounds were generally obtained in moderate yields with a broad range of compatible functionalities.
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http://dx.doi.org/10.1039/d4ob01714e | DOI Listing |
Org Biomol Chem
January 2025
College of Chemistry, Xiangtan University, Xiangtan 411105, China.
Isoxazolidines are structurally important scaffolds in many natural products and bioactive compounds. Herein, we report a novel synthetic method for isoxazolidine derivatives through visible-light-induced photoredox cascade cyclization of nitroarenes with triethylamine under aerobic conditions. The resultant 5-hydroxyl isoxazolidine compounds were generally obtained in moderate yields with a broad range of compatible functionalities.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
October 2024
Department of Chemistry, University of Illinois Chicago 845 West Taylor Street, Chicago, 60607, Illinois, USA.
Electrochemical reduction of 2-allyl-substituted nitroarenes using a simple, undivided electrochemical cell with non-precious electrodes to generate nitroarene radical anions was developed. The nitroarene radical anion intermediates participate in 1,5-hydrogen atom transfer reactions to construct quinoline N-oxides bearing aryl-, heteroaryl-, alkenyl-, benzyl-, sulfonyl-, or carboxyl groups.
View Article and Find Full Text PDFOrg Biomol Chem
July 2024
Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research, S. A. S. Nagar, Punjab 160062, India.
Org Biomol Chem
February 2024
Faculty of Chemical Engineering, Ho Chi Minh City University of Technology (HCMUT), 268 Ly Thuong Kiet Street, District 10, Ho Chi Minh City, Vietnam.
Herein we report a method for affording 2-benzyl benzoxazoles from substituted styrenes and 2-nitrophenols. The success of this method relies on the use of simple reagents, namely elemental sulfur and DABCO. A combination of identical reagents was utilized for the annulation of styrenes with ,-dialkyl-3-nitroanilines to afford 2-benzyl benzothiazoles.
View Article and Find Full Text PDFMolecules
July 2023
Dipartimento di Chimica, Università Degli Studi di Milano, Via C. Golgi 19, 20133 Milano, Italy.
4-Quinolones are the structural elements of many pharmaceutically active compounds. Although several approaches are known for their synthesis, the introduction of an aryl ring in position 2 is problematic with most of them. The reductive cyclization of -nitrochalcones by pressurized CO, catalyzed by ruthenium or palladium complexes, has been previously reported to be a viable synthetic strategy for this aim, but the need for pressurized CO lines and autoclaves has prevented its widespread use.
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